2-(Tri-n-butylstannyl)oxazole → 5-ethyl-2-{4-[(1R,2R)-2-({[4-(1,3-oxazol-2-yl)benzyl]oxy}methyl)cyclopropyl]piperidin-1-yl}pyrimidine

HRID 1468840Notes

Reaction equation

Br[C:2]1[CH:27]=[CH:26][C:5]([CH2:6][O:7][CH2:8][C@@H:9]2[CH2:11][C@@H:10]2[CH:12]2[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][N:19]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:33]1[O:34][CH:35]=[CH:36][N:37]=1)CCC>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:24]([C:21]1[CH:20]=[N:19][C:18]([N:15]2[CH2:16][CH2:17][CH:12]([C@H:10]3[CH2:11][C@H:9]3[CH2:8][O:7][CH2:6][C:5]3[CH:26]=[CH:27][C:2]([C:33]4[O:34][CH:35]=[CH:36][N:37]=4)=[CH:3][CH:4]=3)[CH2:13][CH2:14]2)=[N:23][CH:22]=1)[CH3:25]

Participants

Conditions

Temperature: 90 °C

Procedure

The product of step A (100 mg, 0.2 mmol), Pd(PPh3)2Cl2 (16 mg, 0.02 mmol), and 2-(tributylstannyl)oxazole (125 mg, 0.35 mmol) were dissolved in toluene (2.5 mL), and the solution was heated at 90° C. for 18 h. Silica gel was added, and the slurry was subjected to silica gel column chromatography (2/1 EtOAc/hexanes) to provide the title compound. MS (ESI) m/z 419 [M+H]+. GPR119 Human EC50: 12 nM

Workup

additionSilica gel was added

Sources & evidence

ORD record: ord-148bb1197fed42838750bf94c0f59747
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006228B2

Reaction notes

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