3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester → Methyl 2-((S)-6-((R)-4-(4-(3,6-dihydro-2H-pyran-4-yl)-2,6-dimethylphenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

HRID 237485Notes

Reaction equation

HRID 237485 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:26]2[C:31]([CH3:32])=[CH:30][C:29](I)=[CH:28][C:27]=2[CH3:34])=[C:6]2[C:10]=1[C@H:9]([O:11][C:12]1[CH:25]=[CH:24][C:15]3[C@H:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:17][O:18][C:14]=3[CH:13]=1)[CH2:8][CH2:7]2.[O:35]1[CH2:40][CH:39]=[C:38](B2OC(C)(C)C(C)(C)O2)[CH2:37][CH2:36]1>>[O:35]1[CH2:36][CH:37]=[C:38]([C:29]2[CH:30]=[C:31]([CH3:32])[C:26]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[C:10]4[C:6]=3[CH2:7][CH2:8][C@H:9]4[O:11][C:12]3[CH:25]=[CH:24][C:15]4[C@H:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:17][O:18][C:14]=4[CH:13]=3)=[C:27]([CH3:34])[CH:28]=2)[CH2:39][CH2:40]1

Participants

3

Reactant 2

HCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 86697149Methyl 2-((S)-6-((R)-7-fluoro-4-(4-iodo-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 86697151Methyl 2-((S)-6-((R)-4-(4-(3,6-dihydro-2H-pyran-4-yl)-2,6-dimethylphenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Procedure

The title compound is prepared from methyl 2-((S)-6-((R)-7-fluoro-4-(4-iodo-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane following a procedure analogous to that described in Step 4 of Intermediate 2. LC (method 8): tR=0.92 min; Mass spectrum (ESI+): m/z=551 [M+Na]+.

Sources & evidence

ORD record
ord-bc3197f373b24827bccd1852fc5a10d7
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

Loading…