2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 59619904, compound

HRID 445580Notes

Reaction equation

HRID 445580 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:24])[C:13](=[O:23])[N:14]([C:15]4[C:16]([CH3:22])=[N:17][N:18]([CH3:21])[C:19]=4[CH3:20])[C:5]=3[C:4]=2[CH:3]=1.[OH:25][C:26]1[CH:31]=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][C:27]=1[O:41][CH3:42]>>[OH:25][C:26]1[CH:31]=[CH:30][C:29]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][C:6]4[N:12]([CH3:24])[C:13](=[O:23])[N:14]([C:15]5[C:16]([CH3:22])=[N:17][N:18]([CH3:21])[C:19]=5[CH3:20])[C:5]=4[C:4]=3[CH:3]=2)=[CH:28][C:27]=1[O:41][CH3:42]

Participants

3

Reactant 2

HCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 59619981HCID 59619981, compound2×

Product 1

HCID 59619904HCID 59619904, compound

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-3-methyl-1-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate H, 39 mg, 0.100 mmol) and 4-hydroxy-3-methoxyphenylboronic acid pinacol ester (Aldrich, Buchs, Switzerland, 30 mg, 0.120 mmol) to give the title compound as a lightly yellow foam. (HPLC: tR 2.50 min (Method A); M+H=430 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.23 (s, 1H), 8.93 (s, 1H), 8.06-7.99 (m, 1H), 7.92-7.85 (m, 1H), 7.51-7.46 (m, 1H), 7.03-6.96 (m, 1H), 6.94-6.89 (m, 1H), 6.87-6.81 (m, 1H), 3.85 (s, 3H), 3.79 (s, 3H), 3.58 (s, 3H), 2.08 (s, 3H), 1.94 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-290c5df479244a16bfd006c9734e61b3
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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