(3-Fluorophenyl)(4-hydroxy-3-iodophenyl)methanone → (3-fluorophenyl)(2-{2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)methanone

HRID 1064719Notes

Reaction equation

HRID 1064719 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12](I)[CH:11]=2)=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH2:18]([N:22]1[CH2:26][CH2:25][CH2:24][C@H:23]1[CH3:27])[CH2:19][C:20]#[CH:21]>>[F:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][C:13]3[O:16][C:20]([CH2:19][CH2:18][N:22]4[CH2:26][CH2:25][CH2:24][C@H:23]4[CH3:27])=[CH:21][C:12]=3[CH:11]=2)=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 11325317(3-Fluorophenyl)(4-hydroxy-3-iodophenyl)methanoneHCID 11367023(R)-1-(But-3-yn-1-yl)-2-methylpyrrolidine

Product 1

HCID 9946461(3-fluorophenyl)(2-{2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)methanone

Procedure

The product from Example 69B and a 0.1 M solution of the product from Example 68B were processed as described in Example 68C to provide the title compound. 1HNMR (300 MHz, CD3OD) δ 1.26 (d, 3H, J=6.1 Hz), 1.57 (m, 1H), 1.91 (m, 2H), 2.10-2.63 (m, 2H), 2.87 (m, 2H) 3.18 (m, 2H), 3.42 (m, 2H), 6.76 (s, 1H), 7.37-7.59 (m, 5H), 7.76 (d, 1H, J=8.9 Hz), 7.98 (s, 1H); MS (ESI) m/z 352.1 (M++1).

Sources & evidence

ORD record
ord-d30ca3a055064ced9c0f915166b19155
Source dataset
uspto-grants-2005_11
Patent number
US06969730B2

Reaction notes

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