5-Fluoro-2-methylphenylboronic acid → HCID 53240601, compound

HRID 2375693Notes

Reaction equation

HRID 2375693 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][CH2:17][CH2:18][CH3:19])=[O:15].[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:26]3[CH:25]=[C:24]([F:27])[CH:23]=[CH:22][C:21]=3[CH3:20])[C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:14]([NH:16][CH2:17][CH2:18][CH3:19])=[O:15]

Participants

3

Reactant 2

HCID 27831905-Fluoro-2-methylphenylboronic acidHCID 59791626HCID 59791626, compound

Product 1

HCID 53240601HCID 53240601, compoundYield 58%

Procedure

Using method A, 4-amino-7-fluoro-8-iodo-N-propyl-cinnoline-3-carboxamide (300 mg, 0.80 mmol) and (2-methyl-5-fluorophenyl)boronic acid (246.8 mg, 1.60 mmol) were reacted to afford the title compound (164.7 mg, 58% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.48 (bs, 1H), 7.93 (d×d, J=5.3 Hz, J=9.4 Hz, 1H), 7.54 (apparent t, J=8.6 Hz, 1H), 7.30 (d×d, J=5.6 Hz, J=8.3 Hz, 1H), 6.99-7.09 (m, 2H), 3.44 (apparent q, J=7.0 Hz, 2H), 2.03 (s, 3H), 1.64 (apparent sextet, J=7.4 Hz, 2H), 0.99 (t, J=7.4 Hz, 3H). MS APCI, m/z=357 (M+H) HPLC 2.78 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-8f81e8feb21f42cc85064ac5cb476176
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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