{(S)-6-[(R)-4-Bromomethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester → {(S)-6-[(R)-4-(7,8-Dihydro-[1,6]naphthyridin-6-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

HRID 1422632Notes

Reaction equation

HRID 1422632 reaction equation
[CH3:1][O:2][C:3](=[O:30])[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]([CH2:28]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.[N:31]1[C:40]2[CH2:39][CH2:38][N:37]=[CH:36][C:35]=2[CH:34]=[CH:33][CH:32]=1>>[CH3:1][O:2][C:3](=[O:30])[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]([CH2:28][N:37]5[CH2:38][CH2:39][C:40]6[N:31]=[CH:32][CH:33]=[CH:34][C:35]=6[CH2:36]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 86700813{(S)-6-[(R)-4-Bromomethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl esterHCID 895012817,8-Dihydro-1,6-naphthyridine

Product 1

HCID 90312763{(S)-6-[(R)-4-(7,8-Dihydro-[1,6]naphthyridin-6-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-bromomethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester and 7,8-dihydro-[1,6]naphthyridine following a procedure analogous to that described for Intermediate 42. LC (method 1): tR=1.01 min; Mass spectrum (ESI+): m/z=539 [M+H]+.

Sources & evidence

ORD record
ord-3260879e7e8f4742a0e081c39c0bcd9b
Source dataset
uspto-grants-2015_01
Patent number
US08927531B2

Reaction notes

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