1,3,5-Tribromobenzene → 5-(3,5-Dibromo-phenylamino)-pyridine-2-carbonitrile
Reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[Br:10][C:11]1[CH:16]=[C:15](Br)[CH:14]=[C:13]([Br:18])[CH:12]=1>>[Br:10][C:11]1[CH:16]=[C:15]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=2)[CH:14]=[C:13]([Br:18])[CH:12]=1Participants
Procedure
5-Amino-pyridine-2-carbonitrile was coupled with 1,3,5-tribromobenzene to give 5-(3,5-dibromo-phenylamino)-pyridine-2-carbonitrile by the method described in Example 44. 5-(3,5-Dibromo-phenylamino)-pyridine-2-carbonitrile was converted to [3-bromo-5-(6-cyano-pyridin-3-ylamino)-phenyl]-carbamic acid methyl ester using the conditions in Example 86, replacing methylsulfonamide with carbamic acid methyl ester. [3-Bromo-5-(6-cyano-pyridin-3-ylamino)-phenyl]-carbamic acid methyl ester was converted to [3-(6-cyano-pyridin-3-ylamino)-5-(1H-indol-4-yl)-phenyl]-carbamic acid methyl ester as described in Example 102. 1H NMR (400 MHz, acetone-d6): δ 10.41 (s, 1H), 8.84 (s, 1H), 8.50 (d, J=2.5 Hz, 1H), 8.44 (s, 1H), 7.72-7.63 (m, 4H), 7.46 (d, J=7.6 Hz, 1H), 7.42 (t, J=2.7 Hz, 1H), 7.26 (s, 1H), 7.23-7.14 (m, 2H), 6.75 (s, 1H), 3.73 (s, 3H).
Sources & evidence
- ORD record
- ord-a8bd94637e9242c58bd661a4c37616a5
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504401B2
Reaction notes
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