4-Benzyloxy-3-fluorophenylboronic Acid → (1S,2S)-2-{4-[(R)-4-(4-Benzyloxy-3-fluoro-phenoxy)-7-fluoro-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid ethyl ester

HRID 625689Notes

Reaction equation

HRID 625689 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20]([OH:26])[CH:21]=[CH:22][C:23]=3[F:25])[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)=[O:5])[CH3:2].[CH2:27]([O:34][C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][C:36]=1[F:44])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(OC([C@H]1C[C@@H]1C1C=CC(O[C@H]2C3C(=C(OC4C=CC(OCC5C=CC=CC=5)=CC=4)C=CC=3F)CC2)=CC=1)=O)C>>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:10]=[CH:11][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20]([O:26][C:38]4[CH:39]=[CH:40][C:35]([O:34][CH2:27][C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=5)=[C:36]([F:44])[CH:37]=4)[CH:21]=[CH:22][C:23]=3[F:25])[CH2:18][CH2:17]2)=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 118093712(1S,2S)-2-[4-((R)-7-Fluoro-4-hydroxy-indan-1-yloxy)-phenyl]-cyclopropanecarboxylic acid ethyl ester2×HCID 118093741(1S,2S)-2-{4-[(R)-4-(4-Benzyloxy-phenoxy)-7-fluoro-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 118093721(1S,2S)-2-{4-[(R)-4-(4-Benzyloxy-3-fluoro-phenoxy)-7-fluoro-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid ethyl ester

Procedure

The title compound is prepared from (1S,2S)-2-[4-((R)-7-fluoro-4-hydroxy-indan-1-yloxy)-phenyl]-cyclopropanecarboxylic acid ethyl ester (Intermediate 5, 0.8 g, 2.2 mmol) and 4-benzyloxy-3-fluorophenylboronic acid (2.21 g, 9.0 mmol) in a manner analogous to that described for Intermediate 6 (Yield 0.8 g). LC (METHOD 6): tR=0.96 min; Mass spectrum (ES+): m/z=557 [M+H]+.

Sources & evidence

ORD record
ord-02a3185c6cc942c0b4266d7051898366
Source dataset
uspto-grants-2016_04
Patent number
US09308194B2

Reaction notes

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