1,3,5-Tribromobenzene → HCID 15603181, compound

HRID 1784853Notes

Reaction equation

HRID 1784853 reaction equation
Br[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([Br:9])[CH:3]=1.ClC1C=C(C=CN=1)C#N.[Cl:19][C:20]1[CH:25]=[C:24]([C:26]([C:28]2[CH:29]=[C:30]([NH:53][C:54](=[O:56])[CH3:55])[CH:31]=[C:32]([C:34]3[CH:42]=[CH:41][CH:40]=[C:39]4[C:35]=3[CH:36]=[CH:37][N:38]4[Si](C(C)C)(C(C)C)C(C)C)[CH:33]=2)=[O:27])[CH:23]=[CH:22][N:21]=1>>[Cl:19][C:20]1[CH:25]=[C:24]([C:26]([C:2]2[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([Br:9])[CH:3]=2)=[O:27])[CH:23]=[CH:22][N:21]=1.[Cl:19][C:20]1[CH:25]=[C:24]([C:26]([C:28]2[CH:29]=[C:30]([NH:53][C:54](=[O:56])[CH3:55])[CH:31]=[C:32]([C:34]3[CH:42]=[CH:41][CH:40]=[C:39]4[C:35]=3[CH:36]=[CH:37][NH:38]4)[CH:33]=2)=[O:27])[CH:23]=[CH:22][N:21]=1

Participants

5

Reactant 3

HCID 122791,3,5-TribromobenzeneHCID 5686382-Chloro-4-cyanopyridineHCID 86609397HCID 86609397, compound2×

Product 2

HCID 15603181HCID 15603181, compoundHCID 50994269HCID 50994269, compound

Procedure

(2-Chloro-pyridin-4-yl)-(3,5-dibromo-phenyl)-methanone was prepared from 1,3,5-tribromobenzene and 2-chloro-isonicotinonitrile as described in Example 25. This was converted to N-[3-(2-chloro-pyridine-4-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-acetamide in the same manner as described for Example 82. N-[3-(2-Chloro-pyridine-4-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-acetamide was deprotected to give N-[3-(2-chloro-pyridine-4-carbonyl)-5-(1H-indol-4-yl)-phenyl]-acetamide as described in Example 75. 1H NMR (400 MHz, CD3COCD3): δ 10.48 (s, 1H), 9.53 (s, 1H), 8.63 (d, J=5.0 Hz, 1H), 8.41 (t, J=1.7 Hz, 1H), 8.14 (t, J=1.6 Hz, 1H), 7.82 (t, J=1.5 Hz, 1H), 7.79 (s, 1H), 7.71 (dd, J=5.0, 1.3 Hz, 1H), 7.49 (d, J=7.8 Hz, 1H), 7.43 (t, J=2.8 Hz, 1H), 7.23-7.15 (m, 2H), 6.74 (s, 1H), 2.15 (s, 3H).

Sources & evidence

ORD record
ord-3f1efc668ff44e5e949c0e45a7f3e243
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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