Benzyl carbamate → HCID 15602886, compound

HRID 1784835Notes

Reaction equation

HRID 1784835 reaction equation
C(OC(=O)N)C1C=CC=CC=1.[CH2:12]([O:19][C:20](=[O:55])[NH:21][C:22]1[CH:27]=[C:26]([C:28]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:29]=2[CH:30]=[CH:31][N:32]3[Si](C(C)C)(C(C)C)C(C)C)[CH:25]=[C:24]([C:47]([C:49]2[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=2)=[O:48])[CH:23]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([O:19][C:20](=[O:55])[NH:21][C:22]1[CH:23]=[C:24]([C:47]([C:49]2[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=2)=[O:48])[CH:25]=[C:26]([C:28]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:29]=2[CH:30]=[CH:31][NH:32]3)[CH:27]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 12136Benzyl carbamateHCID 50994358HCID 50994358, compound

Product 1

HCID 15602886HCID 15602886, compound

Procedure

3-Bromo-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid benzyl ester was converted to [3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid benzyl ester, then deprotected to give [3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid benzyl ester by the method of Example 35. 1H NMR (400 MHz, methanol-d4): δ 9.07 (s, 1H), 8.77 (d, J=4.8 Hz, 1H), 8.57 (s, 1H), 8.14 (dt, J=4.9, 2.6 Hz, 1H), 8.08 (s, 1H), 7.84 (s, 1H), 7.77 (t, J=1.5 Hz, 1H), 7.42-7.29 (m, 8H), 7.26-7.13 (m, 3H), 6.69 (s, 1H), 5.20 (s, 2H).

Sources & evidence

ORD record
ord-4ab94aa7f7d849508f04b6631b696316
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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