Phenylboronic Acid → HCID 23629933, compound

HRID 31094Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[C:6](=[C:7](I)[C:8]([Cl: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].[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:8]([Cl: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

Reactant 2

HCID 66827Phenylboronic Acid

HCID 672286764-amino-7-chloro-8-iodo-N-propyl-cinnoline-3-carboxamide

Product 1

HCID 23629933HCID 23629933, compoundYield 56.2%

Procedure

Using Method F, 4-amino-7-chloro-8-iodo-N-propyl-cinnoline-3-carboxamide (184 mg, 0.47 mmol) and phenylboronic acid (229 mg, 1.89 mmol) were reacted (refluxed 40 hours) to afford the title compound (90 mg, 56% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.49 (bs, 1H), 7.82 (d, J=9.0 Hz, 1H), 7.75 (d, J=9.0 Hz, 1H), 7.42-7.55 (m, 5H), 3.43 (apparent q, J=6.6 Hz, 2H), 1.63 (apparent sextet, J=7.2 Hz, 2H), 0.98 (t, J=7.4 Hz, 3H). MS APCI, m/z=341 (M+H) HPLC 2.04 min.

Workup

customwere reacted
temperature(refluxed 40 hours)

Sources & evidence

ORD record: ord-867eb9495aaa4b1caa66442e0c14efec
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425556B2

Reaction notes

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