4-(Hydroxymethyl)benzeneboronic acid → HCID 90036695, compound

HRID 925843Notes

Reaction equation

HRID 925843 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=[CH:7][C:6]=2[CH:5]=[C:4]([C:16]#[N: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>>[OH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]4=[CH:7][C:6]=3[CH:5]=[C:4]([C:16]#[N:17])[CH:3]=2)=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 90035900HCID 90035900, compound2×

Product 1

HCID 90036695HCID 90036695, compound

Procedure

The title compound, light brown solid (18 mg, 23%), MS (ISN) m/z=318.5 [(M+H)+], mp 257.5° C., was prepared in accordance with the general method of example 1 from 6-bromo-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-8-carbonitrile (intermediate 15) (72.5 mg, 0.25 mmol) and commercially available 4-hydroxymethyl-phenylboronic acid (49.4 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-dc900d071d2e426aaddaa6420782e241
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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