(3-hydroxyphenyl)boronic Acid → HCID 57736644, compound

HRID 2218730Notes

Reaction equation

HRID 2218730 reaction equation
Br[CH:2]=[C:3]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2.[OH:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1>>[N:10]1[CH:11]=[CH:12][CH:13]=[C:8]2[CH2:7][CH2:6][C:5]3[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=3/[C:3](=[CH:2]\[C:23]3[CH:24]=[C:19]([OH:18])[CH:20]=[CH:21][CH:22]=3)/[C:9]=12

Participants

3

Reactant 2

HCID 2734359(3-hydroxyphenyl)boronic AcidHCID 68934737HCID 68934737, compound

Product 1

HCID 57736644HCID 57736644, compoundYield 63.7%

Procedure

Following procedures essentially as described in Example 219, combine 11-bromomethylene-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (250 mg, 0.87 mmol) and (3-hydroxyphenyl) boronic acid (133 mg, 0.96 mmol). Purify to provide product 166 mg (63%) as an off-white solid. LC/MS: 300.1 (M+H). 1H NMR (DMSO, 400 MHz): δ9.22 (s,1H), 8.40 (d,1H), 7.49 (d,1H), 7.34 (d,1H), 7.24 (d,1H), 7.21 (d,3H), 7.15 (s,1H), 7.04 (t,1H), 6.92 (d,1H), 6.90 (d,1H), 6.52 (d,1H), 6.40-6.42 (m,2H), 3.4-2.8 (m,4H).

Workup

  1. customPurify

Sources & evidence

ORD record
ord-376661e7f7534d36a577477a51ab75e2
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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