2-Methoxyphenylboronic acid → 4-(2-Methoxyphenyl)-6-[3,5-bis(trifluoromethyl)benzyl]-6,7,8,9-tetrahydro-5H-10-oxa-1,6-diazabenzocyclooctene-5-one

HRID 1795001Notes

Reaction equation

HRID 1795001 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][O:11][C:10]2[N:15]=[CH:16][CH:17]=[C:18](I)[C:9]=2[C:8]1=[O:20].[CH3:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1B(O)O>>[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][O:11][C:10]2[N:15]=[CH:16][CH:17]=[C:18]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[O:31][CH3:30])[C:9]=2[C:8]1=[O:20]

Participants

3

Reactant 2

HCID 27339582-Methoxyphenylboronic acidHCID 114780954-Iodo-6-[3,5-bis(trifluoromethyl)benzyl]-6,7,8,9-tetrahydro-5H-10-oxa-1,6-diazabenzocyclooctene-5-one

Product 1

HCID 221844314-(2-Methoxyphenyl)-6-[3,5-bis(trifluoromethyl)benzyl]-6,7,8,9-tetrahydro-5H-10-oxa-1,6-diazabenzocyclooctene-5-oneYield 86%

Procedure

In a similar manner to Reference Example 5, 5-[3,5-bis(trifluoromethyl)benzyl]-7-iodo6-oxo-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine (compound of Reference Example 3; 2.00 g) was reacted with 2-methoxyphenylboronic acid (690 mg) to obtain 5-[3,5-bis(trifluoromethyl)benzyl]-7-(2-methoxyphenyl)-6-oxo-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine (1.65 g, 86%).

Sources & evidence

ORD record
ord-ff8c1bc3a4e5400abda0e11c2a2cd45f
Source dataset
uspto-grants-2006_04
Patent number
US07026309B2

Reaction notes

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