4-(Hydroxymethyl)benzeneboronic acid → HCID 90035995, compound

HRID 925892Notes

Reaction equation

HRID 925892 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]([C:17]#[N:18])[CH:3]=1.[OH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>>[OH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]4=[C:7]([CH3:16])[C:6]=3[CH:5]=[C:4]([C:17]#[N:18])[CH:3]=2)=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 90036297HCID 90036297, compound2×

Product 1

HCID 90035995HCID 90035995, compound

Procedure

The title compound, grey solid (68 mg, 82%), MS (ISP) m/z=332.5 [(M+H)+], mp 265° C., was prepared in accordance with the general method of example 1 from 6-bromo-10-methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-8-carbonitrile (intermediate 16) (76 mg, 0.25 mmol) and commercially available 4-hydroxymethyl-phenylboronic acid (49.4 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-ef5f166d69dc48999999dd5808e44231
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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