4-(3-Bromo-5-triisopropylsilanyloxy-phenylamino)-benzonitrile → 5-[3-hydroxy-5-(1H-indol-4-yl)-phenylamino]-pyridine-2-carbonitrile

HRID 1784851Notes

Reaction equation

HRID 1784851 reaction equation
BrC1C=C(NC2C=CC(C#N)=CC=2)C=C(O[Si](C(C)C)(C(C)C)C(C)C)C=1.C([Si](C(C)C)(C(C)C)[N:32]1[C:40]2[C:35](=[C:36]([C:41]3[CH:42]=[C:43]([NH:58][C:59]4[CH:60]=[CH:61][C:62]([C:65]#[N:66])=[N:63][CH:64]=4)[CH:44]=[C:45]([O:47][Si](C(C)C)(C(C)C)C(C)C)[CH:46]=3)[CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33]1)(C)C>>[OH:47][C:45]1[CH:44]=[C:43]([NH:58][C:59]2[CH:60]=[CH:61][C:62]([C:65]#[N:66])=[N:63][CH:64]=2)[CH:42]=[C:41]([C:36]2[CH:37]=[CH:38][CH:39]=[C:40]3[C:35]=2[CH:34]=[CH:33][NH:32]3)[CH:46]=1

Participants

3

Reactant 2

HCID 688441304-(3-Bromo-5-triisopropylsilanyloxy-phenylamino)-benzonitrileHCID 688460775-[3-(1-triisopropylsilanyl-1H-indol-4-yl)-5-triisopropylsilanyloxy-phenylamino]-pyridine-2-carbonitrile

Product 1

HCID 156029935-[3-hydroxy-5-(1H-indol-4-yl)-phenylamino]-pyridine-2-carbonitrile

Procedure

4-(3-Bromo-5-triisopropylsilanyloxy-phenylamino)-benzonitrile was converted to 5-[3-(1-triisopropylsilanyl-1H-indol-4-yl)-5-triisopropylsilanyloxy-phenylamino]-pyridine-2-carbonitrile, and the triisopropylsilyl groups were removed with tetra n-butylammonium fluoride to give 5-[3-hydroxy-5-(1H-indol-4-yl)-phenylamino]-pyridine-2-carbonitrile as described in Example 35. 1H NMR (400 MHz, CD3OD) δ 8.31 (dd, J=2.8, 0.4 Hz, 1H), 7.57 (dd, J=8.8, 0.8 Hz, 1H), 7.49 (dd, J=8.8, 2.8 Hz, 1H), 7.35 (m, 1H), 7.26 (d, J=3.2 Hz, 1H), 7.14 (t, J=7.6 Hz, 1H), 7.05 (dd, J=7.2, 1.2 Hz, 1H), 6.97 (m, 1H), 6.89 (dd, J=2.4, 1.6 Hz, 1H), 6.66 (m, 1H), 6.61 (m, 1H).

Workup

  1. customthe triisopropylsilyl groups were removed with tetra n-butylammonium fluoride

Sources & evidence

ORD record
ord-e668e222400e4a6f880d1188d108b5b3
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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