3-Hydroxyphenacyl bromide → HCID 59283019, compound

HRID 1965850Notes

Reaction equation

HRID 1965850 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([NH2:12])=[N:8][NH:9]2)=[CH:5][CH:4]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=1)=O>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:8]([CH:14]=[C:15]([C:17]4[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=4)[N:12]=3)[NH:9][C:10]=2[CH:11]=1

Participants

3

Reactant 2

HCID 69172063-Hydroxyphenacyl bromideHCID 214091926-Methoxy-1H-indazol-3-amine

Product 1

HCID 59283019HCID 59283019, compound

Procedure

Compound 3-(7-methoxy-5H-imidazo[1,2-b]indazol-2-yl)phenol (W298) was prepared using the general procedure for cyclization between 6-methoxy-1H-indazol-3-amine (80 mg, 0.5 mmol) and 2-bromo-1-(3-hydroxyphenyl)ethanone (107 mg, 0.55 mmol), as a white solid (40 mg, 22%). 1H NMR (400 MHz, DMSO-d6) δ 9.84 (brs, 1 H), 8.63 (s, 1 H), 7.85 (d, J=9.2 Hz, 1 H), 7.36 (t, J=8.0 Hz, 1 H), 7.31-7.29 (m, 1 H), 7.24 (t, J=2.0 Hz, 1 H), 7.13 (d, J=2.0 Hz, 1 H), 6.99 (dd, J=9.2, 2.0 Hz, 1 H), 6.88 (m, 1 H), 3.90 (s, 3 H); MS (ESI) m/z 280 (M+H+).

Sources & evidence

ORD record
ord-7eaf8c8fb2e8424987dd406499eee908
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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