{(S)-6-[(R)-4-bromo-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester → {(S)-6-[(R)-4-(2,2-Dimethyl-morpholin-4-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

HRID 1422626Notes

Reaction equation

HRID 1422626 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19](Br)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1.[CH3:30][C:31]1([CH3:42])[O:36][CH2:35][CH2:34][NH+:33]([CH2:37][B-](F)(F)F)[CH2:32]1>>[CH3:1][O:2][C:3](=[O:29])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([CH2:37][N:33]5[CH2:34][CH2:35][O:36][C:31]([CH3:42])([CH3:30])[CH2:32]5)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1

Participants

3

Reactant 2

HCID 86700774{(S)-6-[(R)-4-bromo-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl esterHCID 90313525HCID 90313525, compound

Product 1

HCID 90313415{(S)-6-[(R)-4-(2,2-Dimethyl-morpholin-4-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Procedure

The title compound is prepared from {(S)-6-[(R)-4-bromo-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester and (2,2-dimethyl-morpholinium-4-yl)methyltrifluoroborate following a procedure analogous to that described for Intermediate 3. LC (method 3): tR=1.27 min; Mass spectrum (ESI+): m/z=520 [M+H]+.

Sources & evidence

ORD record
ord-af0bb56fba7247f0a788e82635926a3d
Source dataset
uspto-grants-2015_01
Patent number
US08927531B2

Reaction notes

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