Benzoic acid, 3,5-dibromo- → HCID 50994513, compound

HRID 1784869Notes

Reaction equation

HRID 1784869 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:11])[CH:10]=1)[C:5]([OH:7])=O.[NH2:12][C:13]1[C:18](O)=[CH:17][CH:16]=[CH:15][N:14]=1>>[Br:11][C:9]1[CH:8]=[C:4]([C:5]2[O:7][C:18]3[C:13]([N:12]=2)=[N:14][CH:15]=[CH:16][CH:17]=3)[CH:3]=[C:2]([Br:1])[CH:10]=1

Participants

3

Reactant 2

HCID 12063Benzoic acid, 3,5-dibromo-HCID 281142-Amino-3-Hydroxypyridine

Product 1

HCID 50994513HCID 50994513, compound

Procedure

3,5-Dibromo-benzoic acid and 2-amino-pyridin-3-ol were condensed to give 2-(3,5-dibromo-phenyl)-oxazolo[4,5-b]pyridine using the conditions of Clark, R. L., et al., J. Med. Chem. 21: 1158-62 (1978). This compound was converted to N-(3-bromo-5-oxazolo[4,5-b]pyridin-2-yl-phenyl)-acetamide as described in Example 82. Conversion to N-[3-(1H-Indol-4-yl)-5-oxazolo[4,5-b]pyridin-2-yl-phenyl]-acetamide was carried out as described in Example 75. 1H NMR (400 MHz, CD3OD): δ 8.39-8.43 (m, 2H), 8.28 (d, J=1.4 Hz, 1H), 8.15 (t, J=1.7 Hz, 1H), 7.95 (dt, J=4.7, 2.7 Hz, 1H), 7.38-7.41 (m, 1H), 7.30-7.34 (m, 1H), 7.25 (d, J=3.1 Hz, 1H), 7.14-7.17 (m, 2H), 6.67 (d, J=3.1 Hz, 1H), 2.13 (s, 3H).

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-4708cdf3136740148e74c87a84be9659
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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