Reaction SMILES: [Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([NH2:11])[C:3]=1I.[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15]>>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([NH2:11])[C:3]=1[C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13]
Reactant: Nc1ncc([N+](=O)[O-])c(Cl)c1I
Reactant: C#C[Si](C)(C)C
Product: C[Si](C)(C)C#Cc1c(N)ncc([N+](=O)[O-])c1Cl

Procedure:
Methods for preparing 1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine compounds of the invention are illustrated in Scheme VIII. As shown in step a, 4-chloro-3-iodopyridin-2-amine 52 may be nitrated to give 4-chloro-3-iodo-5-nitropyridin-2-amine 53 as described in Example #21 or in Larock, R. C. “Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd edition”, 1999, Wiley-VCH. 4-Chloro-3-iodo-5-nitropyridin-2-amine 53 is reacted with a (trimethylsilyl)acetylene via a Sonogashira cross coupling using methods known to one skilled in the art (for example Example #21 or WO2006058120A1) to give 4-chloro-5-nitro-3-((trimethylsilyl)ethynyl)pyridin-2-amine 54 (Scheme VIII, step b). As shown in step c, 4-chloro-5-nitro-3-((trimethylsilyl)ethynyl)pyridin-2-amine 54 is deprotected to give the 4-chloro-3-ethynyl-5-nitropyridin-2-amine 55 as described in Example #21 or using methods known to one skilled in the art (for example, the books from Greene, T. W. and Wuts, P. G. M. “Protective Groups in Organic Synthesis, 3rd Edition”, 1999, Wiley-Interscience or Larock, R. C. referenced above). 4-Chloro-3-ethynyl-5-nitropyridin-2-amine 55 is cyclized, as shown in step d, to give 4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine 56 as described in Example #21, or by methods known to one skilled in the art (for example, as described in WO2008004117). As shown in step e, amino-substituted 1H-pyrrolo[2,3-b]pyridines 57 are prepared using methods known to one skilled in the art (for example, Example #21 or Larock, R. C. referenced above). Diamino-substituted 1H-pyrrolo[2,3-b]pyridines 58 (Scheme VIII, step f) are prepared from the reduction of nitro-containing 1H-pyrrolo[2,3-b]pyridines 57 using methods known to one skilled in the art (for example, Example #21, General Procedure BBB, or Larock, R. C. referenced above). As shown in step g, diamino-substituted 1H-pyrrolo[2,3-b]pyridines 58 can be cyclized as described in Example #21 or General Procedure DDD to give 1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridines 59. Further functionalization of the R group in 1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridines 59 can be performed, if desired, using reactions known to one skilled in the art (for example, Larock, R. C. referenced above). For example, amides, ureas, sulfonamides, aryl amines, heteroaryl amines, sulfonyl ureas, substituted amines, squaramides, or guanidines can be prepared from 1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine 59 with an R group containing a primary or secondary amine (for example General Procedures G, H, I, J, J.1, XXX, EEEE, K, K.1, L, DD, QQ, RR, YY, ZZ followed by AAA, CCC, YYY, X, X.1, TTTT, or EEEEE). Also, deprotection of the R group in 1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridines 59 to yield an unprotected compound can be performed using conditions such as those described in Greene, T. W. and Wuts, P. G. M. referenced above or in General Procedures E, E.1, F, F.1, Y, or BB. For example, a protecting group such as a benzyloxycarbonyl (Cbz) group can be removed from a protected amine to yield the unprotected amine (for example General Procedures F, F.1, or Y) and the deprotected compounds 59 may then be reacted further as described above. Alternatively, intermediates 56 or 57 may be sulfonamide protected using reactions known to one skilled in the art (for example, Greene, T. W. and Wuts, P. G. M. referenced above or General Procedure K.1) to give sulfonamides 134 and 135 respectively (Scheme VII, steps h and m). As shown in step i, amino-substituted 1H-pyrrolo[2,3-b]pyridines 135 may also be prepared from chloro-substituted 1H-pyrrolo[2,3-b]pyridines 134 using methods known to one skilled in the art (for example, Example #23 or Larock, R. C. referenced above). Diamino-substituted 1H-pyrrolo[2,3-b]pyridines 136 are prepared from the reduction of nitro-containing 1H-pyrrolo[2,3-b]pyridines 135 using methods known to one skilled in the art (for example, Example #23, General Procedure BBB, or Larock, R. C. referenced above). As shown in step k, diamino-substituted 1H-pyrrolo[2,3-b]pyridines 136 can be cyclized as described in Example #23 or General Procedure DDD to give sulfonamide-protected 1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridines 137. Deprotection of the sulfonamide of compounds 137 to yield 1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridines 59 (Scheme VIII, step 1) can be performed using conditions such as those described in Greene, T. W. and Wuts, P. G. M. “Protective Groups in Organic Synthesis, 3rd Edition”, 1999, Wiley-Interscience, General Procedures D, XXX, AAAA, BBBB, or CCCC or Example #23.