Boron tribromide → 6-Hydroxy-4-(4,4,4-trifluoro-butyl)-isoquinoline

HRID 1022874

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[N:8][CH:7]=[C:6]2[CH2:13][CH2:14][CH2:15][C:16]([F:19])([F:18])[F:17].B(Br)(Br)Br.BrC1C=C2C(C=CN=C2)=CC=1O>>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[N:8][CH:7]=[C:6]2[CH2:13][CH2:14][CH2:15][C:16]([F:19])([F:17])[F:18]

Participants

Reactant 3

HCID 25134Boron tribromide

HCID 576470536-Methoxy-4-(4,4,4-trifluoro-butyl)-isoquinoline

HCID 1358548376-Isoquinolinol, 7-bromo-

Product 1

HCID 1360928996-Hydroxy-4-(4,4,4-trifluoro-butyl)-isoquinolineYield 42.4%

Procedure

1.02 g of 6-Methoxy-4-(4,4,4-trifluoro-butyl)-isoquinoline (87) were treated with boron tribromide as described for the synthesis of compound 1 to give 410 mg of the desired product 88. LCMS Method #1, retention time 1.04 min, detected mass 256.00 [M+H]+

Sources & evidence

ORD record: ord-dd086d6d87324607b9f3a4aaf670a77a
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722671B2

Linked notes

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