3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester → HCID 117727985, compound

HRID 1772750Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][C:17]([C:20]3[N:25]4[CH:26]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:28]=[C:24]4[C:23](Cl)=[N:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:35]1[CH2:40][CH:39]=[C:38](B2OC(C)(C)C(C)(C)O2)[CH2:37][CH2:36]1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][C:17]([C:20]3[N:25]4[CH:26]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:28]=[C:24]4[C:23]([C:38]4[CH2:39][CH2:40][O:35][CH2:36][CH:37]=4)=[N:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

HCID 117728364HCID 117728364, compound

Product 1

HCID 117727985HCID 117727985, compoundYield 44%

Procedure

Compound 90g (1.08 g, 2.10 mmol) was subjected to Suzuki coupling with 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane using the method described in Example 87, Step D to obtain compound 90h as a yellow solid (520 mg, 44% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C28H34N6O5: 535.3 (M+H). found: 535.6.

Sources & evidence

ORD record: ord-f03f36dc64974fdd83e50428729276f4
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249163B2

Reaction notes

Loading…