[2-(Benzyloxy)-5-methylphenyl]boronic acid → HCID 89544105, compound

HRID 2203451Notes

Reaction equation

HRID 2203451 reaction equation
BrC1N2C=NC=C2C(=O)N(CC2C=CC(OC)=CC=2)C=1.[CH:21]([N:34]1[C:38]2[CH:39]=[C:40](Br)[CH:41]=[CH:42][C:37]=2[O:36][C:35]1=[O:44])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.ClC1C=CC(O)=C(B(O)O)C=1.[CH2:56]([O:63][C:64]1[CH:69]=[CH:68][C:67]([CH3:70])=[CH:66][C:65]=1B(O)O)[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>>[CH:21]([N:34]1[C:38]2[CH:39]=[C:40]([C:69]3[CH:68]=[C:67]([CH3:70])[CH:66]=[CH:65][C:64]=3[O:63][CH2:56][C:57]3[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=3)[CH:41]=[CH:42][C:37]=2[O:36][C:35]1=[O:44])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 14631588[2-(Benzyloxy)-5-methylphenyl]boronic acidHCID 23005362(5-Chloro-2-hydroxyphenyl)boronic Acid (contains varying amounts of Anhydride)HCID 895440475-bromo-7-(4-methoxybenzyl)imidazo[1,5-a]pyrazin-8(7H)-oneHCID 89544282HCID 89544282, compound

Product 1

HCID 89544105HCID 89544105, compound

Procedure

Following the procedure as described in EXAMPLE 4 and making non-critical variations to replace 5-bromo-7-(4-methoxybenzyl)imidazol[1,5-a]pyrazin-8(7H)-one with 3-benzhydryl-5-bromobenzo[d]oxazol-2(3H)-one and (5-chloro-2-hydroxyphenyl)boronic acid with (2-(benzyloxy)-5-methylphenyl)boronic acid, 3-benzhydryl-5-(2-(benzyloxy)-5-methylphenyl)benzo[d]oxazol-2(3H)-one was obtained as a colorless solid in quantitative yield (1.05 g): 1H NMR (300 MHz, CDCl3) δ7.30-7.16 (m, 17H), 6.98 (dd, J=8.3, 1.7 Hz, 1H), 6.80-6.76 (m, 3H), 6.68 (s, 1H), 4.95 (s, 2H), 2.24 (s, 3H); MS (ES+) m/z 497.8 (M+1).

Sources & evidence

ORD record
ord-01a8611199ab4a46a8d8c092dbc35830
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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