(2-Fluoro-4-methoxyphenyl)boronic acid → HCID 53240598, compound

HRID 2375692Notes

Reaction equation

HRID 2375692 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].[F:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:22]3[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:21]=3[F: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 15789384(2-Fluoro-4-methoxyphenyl)boronic acidHCID 59791626HCID 59791626, compound

Product 1

HCID 53240598HCID 53240598, compoundYield 67%

Procedure

Using method A, 4-amino-7-fluoro-8-iodo-N-propyl-cinnoline-3-carboxamide (250.0 mg, 0.67 mmol) and (2-fluoro-4-methoxyphenyl)boronic acid (227.1 mg, 1.336 mmol) were reacted to afford the title compound (165.4 mg, 67% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ 8.51 (bs, 1H), 7.90 (d×d, J=5.5 Hz, J=9.2 Hz, 1H), 7.53 (apparent triplet, J=8.9 Hz, 1H), 7.41 (t, J=8.5 Hz, 1H), 6.86 (d×d, J=2.4 Hz, J=8.5 Hz, 1H), 6.80 (d×d, J=2.4 Hz, J=11.6 Hz, 1H), 3.87 (s, 3H), 3.44 (q, J=6.7 Hz, J=12.8 Hz, 2H), 1.65 (apparent sextet, J=7.3 Hz, 2H), 1.00 (t, J=7.3 Hz, 3H). MS APCI, m/z=373 (M+H) HPLC 2.78 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-5aff6cea5f504e70a43b760d83288b4d
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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