Sodium hydride → HCID 68819124, compound

HRID 735563Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1.[C:13]([C:15]1[CH:16]=[C:17]([NH:26][C:27](=O)[O:28]C2C=CC=CC=2)[CH:18]=[CH:19][C:20]=1[S:21]([CH2:24][CH3:25])(=[O:23])=[O:22])#[N:14]>C1COCC1>[C:13]([C:15]1[CH:16]=[C:17]([NH:26][C:27](=[O:28])[O:12][CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([Br:3])=[CH:5][CH:6]=2)[CH:18]=[CH:19][C:20]=1[S:21]([CH2:24][CH3:25])(=[O:23])=[O:22])#[N:14]

Participants

Conditions

Temperature: -40 °C

Procedure

NaH (138 mg, 3.45 mmol, 60% dispersion in oil) was added to a solution of 2-(4-bromophenyl)ethanol (833 mg, 4.1 mmol) in THF (7 mL) at 0° C. and stirred for 10 min. The mixture was cooled to −40° C. and 25A (500 mg, 1.38 mmol) in THF (7 mL) was added. After stirring warming to 0° C. over 1 h and stirring at 0° C. for 3 h the mixture was partitioned between EtOAc and brine (100 mL each). The layers were separated and the organic layer washed with 5% NaOH, brine and concentrated in vacuo. The crude solid was purified by flash chromatrography (0% to 50% EtOAc in Hexanes) to yield 26A (600 mg, 99%) as a white solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.12 (t, J=7.47 Hz, 2 H) 2.95 (t, J=6.59 Hz, 2 H) 3.38 (q, J=7.18 Hz, 2 H) 4.36 (t, J=6.59 Hz, 2 H) 7.27 (d, J=8.35 Hz, 2 H) 7.92 (dd, 1 H) 8.00 (d, 1 H) 8.08 (d, J=2.20 Hz, 1 H) 10.51 (s, 1 H).

Workup

stirringAfter stirring
temperaturewarming to 0° C. over 1 h
stirringstirring at 0° C. for 3 h the mixture
customwas partitioned between EtOAc and brine (100 mL each)
customThe layers were separated
washthe organic layer washed with 5% NaOH, brine
concentrationconcentrated in vacuo
customThe crude solid was purified by flash chromatrography (0% to 50% EtOAc in Hexanes)

Sources & evidence

ORD record: ord-52ab09e731eb473b9831c11f3c710890
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592331B2

Reaction notes

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