Hexane → HCID 10577002, compound

HRID 609824Notes

Reaction equation

HRID 609824 reaction equation
CN(C)[C:3]1[S:4][C:5]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:6]=2[C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:12][CH:11]=1)=[O:9].[F:32][C:33]1[CH:34]=[C:35]([Mg]Br)[CH:36]=[CH:37][CH:38]=1.CCCCCC.C(OCC)(=O)C>C1COCC1.CO>[F:32][C:33]1[CH:38]=[C:37]([C:3]2[S:4][C:5]3[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:6]=3[C:7]=2[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:12][CH:11]=2)=[O:9])[CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 9954835[2-Dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanoneHCID 178505773HCID 178505773, compound

Product 1

HCID 10577002HCID 10577002, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

By the method described in Example 1, [2-dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone (1.5 g, 3.4 mmol) in THF (13 mL) was treated with a 1.9 M THF solution of 3-Fluorophenylmagnesium bromide (9.0 mL, 17 mmol) to provide, after chromatography (silica gel, 1:1 hexane:ethyl acetate, 0-10% MeOH) 1.13 g (68%) of the title compound as an off-white solid: 1H NMR d 1.44 (m, 2H), 1.58 (m, 4H), 2.47 (m, 4H), 2.73 (t, J=6.0 Hz, 2H), 3.89 (s, 3H), 4.08 (t, J=6.0 Hz, 2H), 6.78 (d, J=8.8 Hz, 2H), 6.87-6.93 (m, 1H), 6.97 (dd, J=2.3, 8.9 Hz, 1H), 7.11-7.20 (m, 3H), 7.33 (d, J=2.3 Hz, 1H), 7.53 (d, J=8.9 Hz, 1H), 7.75 (d, J=8.8 Hz, 2H); 13C NMR d 24.2, 25.9, 55.1, 55.7, 57.7, 66.3, 104.3, 104.5, 114.3, 115.15, 115.22, 115.4, 124.4, 124.6, 124.8, 130.3, 132.2, 132.4, 133.7, 140.4, 158.1, 160.9, 163.3, 164.2, 192.8; IR (CHCl3) 1648, 1599 cm-1 ; MS (FD) m/e 489 (M+); Anal. calc'd. for C29H28FNO3S: C, 71.14; H, 5.76; N, 2.86. Found: C, 70.89; H, 5.83; N, 2.85.

Workup

  1. customto provide

Sources & evidence

ORD record
ord-65410dfc10db4817b8f74768f5a488f6
Source dataset
uspto-grants-1999_12
Patent number
US05998442

Reaction notes

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