4-(Hydroxymethyl)benzeneboronic acid → HCID 73335311, compound

HRID 925747Notes

Reaction equation

HRID 925747 reaction equation
Br[C:2]1[C:10]2[N:9]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]3=[C:7]([CH3:16])[C:6]=2[CH:5]=[C:4]([F:17])[CH:3]=1.[OH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1>>[F:17][C:4]1[CH:3]=[C:2]([C:23]2[CH:24]=[CH:25][C:20]([CH2:19][OH:18])=[CH:21][CH:22]=2)[C:10]2[N:9]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]3=[C:7]([CH3:16])[C:6]=2[CH:5]=1

Participants

3

Reactant 2

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 90036178HCID 90036178, compound2×

Product 1

HCID 73335311HCID 73335311, compound

Procedure

The title compound, white solid (59 mg, 73%), MS (ISP) m/z=325.5 [(M+H)+], mp 220° C., was prepared in accordance with the general method of example 1 from 6-bromo-8-fluoro-10-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (intermediate 14) (74.3 mg, 0.25 mmol) and commercially available 4-hydroxymethyl-phenylboronic acid (49.4 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-2d21425ceb1f47c0864e41c029a7bd80
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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