(2-Methoxy-5-methylphenyl)boronic acid → 4-amino-N-cyclopropyl-7-fluoro-8-(2-methoxy-5-methylphenyl)cinnoline-3-carboxamide

HRID 2375713Notes

Reaction equation

HRID 2375713 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](I)[C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:14]([NH:16][CH:17]1[CH2:19][CH2:18]1)=[O:15].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:23]3[CH:24]=[C:25]([CH3:28])[CH:26]=[CH:27][C:22]=3[O:21][CH3:20])[C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:14]([NH:16][CH:17]1[CH2:19][CH2:18]1)=[O:15]

Participants

3

Reactant 2

HCID 2773485(2-Methoxy-5-methylphenyl)boronic acidHCID 672285864-amino-7-fluoro-8-iodo-N-cyclopropyl-cinnoline-3-carboxamide

Product 1

HCID 597915294-amino-N-cyclopropyl-7-fluoro-8-(2-methoxy-5-methylphenyl)cinnoline-3-carboxamideYield 76.2%

Procedure

Using Method A, 4-amino-7-fluoro-8-iodo-N-cyclopropyl-cinnoline-3-carboxamide (178 mg, 0.48 mmol) and 2-methoxy-5-methylphenylboronic acid (160 mg, 0.96 mmol) were reacted. After purification the title compound (134 mg, 76% yield) was obtained as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 8.98 (d, J=4.8 Hz, 1H), 8.50 (a dd, J=5.5, 9.3 Hz, 1H), 7.71 (t, J=9.1 Hz, 1H), 7.23 (m, 1H), 7.106(s, 1H), 7.02 (d, J=8.4 Hz, 1H), 3.60 (s, 3H), 2.95 (m, 1H), 2.28 (s, 3H), 0.67 (m, 4H). MS APCI, m/z=367.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c494f4da35704a6ab6f5fb93979e8237
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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