Sodium hydride → HCID 23678526, compound

HRID 1006289Notes

Reaction equation

[H-].[Na+:2].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][CH2:23][O:24][CH2:25][CH:26]4[CH2:28][CH2:27]4)[CH:20]=3)[N:15]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=3)[C:14]=2[C:38]([OH:40])=[O:39])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4]>O1CCCC1>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][CH2:23][O:24][CH2:25][CH:26]4[CH2:27][CH2:28]4)[CH:20]=3)[N:15]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=3)[C:14]=2[C:38]([O-:40])=[O:39])=[CH:9][CH:8]=1)([CH3:6])([CH3:4])[CH3:5].[Na+:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (6.8 mg, 0.28 mmol) was added to a cooled (0° C.) and stirred solution of 3-(4-tert-butylphenyl)-5-[2-(cyclopropylmethoxy)ethyl]-1-(3-methoxybenzyl)-1H-indole-2-carboxylic acid (Example 275, 145 mg, 0.283 mmol) in tetrahydrofuran (10 mL). The cold bath was removed and the mixture was stirred 2 h. Concentration in vacuo left 148 mg (98%) of the desired product. The product had: 1H NMR (300 MHz, acetone-D6) δ 7.63 (d, 2 H), 7.47 (s, 1 H), 7.34 (d, 2 H), 7.18 (d, 1 H), 7.09(dd, 1 H), 6.96 (dd, 1 H), 6.91 (s, 1 H), 6.85 (d, 1 H), 6.69 (dd, 1 H), 5.75 (s, 2 H), 3.66 (s, 3 H), 3.56 (t, 2 H), 3.22 (d, 2 H), 2.84 (t, 2 H), 1.32 (s, 9 H), 0.89-1.05 (m, 1 H), 0.35-0.45 (m, 2 H), 0.07-0.17 (m, 2 H); mass spectroscopy gave M+2H+−Na=512.2 (calcd exact mass for C33H36NNaO4=533.25).

Workup

customThe cold bath was removed
concentrationConcentration in vacuo
waitleft 148 mg (98%) of the desired product
custommass spectroscopy gave M+2H+−Na=512.2 (calcd exact mass for C33H36NNaO4=533.25)

Sources & evidence

ORD record: ord-d538e1bdd4f04f61b57620649409bc3a
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06787651B2

Reaction notes

Loading…