1-Bromo-2-methylpropane → HCID 45274608, compound

HRID 1667245Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH2:13][N:14]3[CH2:19][CH2:18][CH2:17][C:16]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:15]3=[O:32])[O:10][N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:40][CH:41]([CH3:43])[CH3:42]>CN(C)C=O>[CH2:40]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[C:11]([CH2:13][N:14]3[CH2:19][CH2:18][CH2:17][C:16]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:15]3=[O:32])[O:10][N:9]=2)=[CH:6][CH:7]=1)[CH:41]([CH3:43])[CH3:42]

Participants

Conditions

Temperature: 75 °C

Procedure

To 1-{[3-(4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl]methyl}-3,3-diphenylpiperidin-2-one (Example 206, 0.040 g, 0.094 mmol) and potassium carbonate (0.019 g, 0.141 mmol) in N,N-dimethylformamide (0.5 mL) was added 1-bromo-2-methylpropane (0.012 mL, 0.113 mmol) and the reaction heated to 75° C. for 3 hours. The reaction was cooled, loaded onto a GraceResolv™ 12 g silica gel column (Grace Davison Discovery Sciences) and the product eluted with a gradient of 5% ethyl acetate/hexanes to 40% ethyl acetate/hexanes (Flow=35 mL/minute) over 30 minutes to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.11-7.94 (m, 2H), 7.39-7.13 (m, 10H), 7.06-6.93 (m, 2H), 4.90 (s, 2H), 3.80 (d, J=6.5, 2H), 3.61 (t, J=6.5, 2H), 2.77-2.62 (m, 2H), 2.13 (dp, J=6.8, 13.4, 1H), 2.01-1.80 (m, 2H), 1.04 (t, J=10.1, 6H); MS (ESI+) m/z 482.3 (M+H)+.

Workup

temperatureThe reaction was cooled
washthe product eluted with a gradient of 5% ethyl acetate/hexanes to 40% ethyl acetate/hexanes (Flow=35 mL/minute) over 30 minutes

Sources & evidence

ORD record: ord-1a86bf5b2c81494aac3ad57f19c2e380
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044069B2

Reaction notes

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