Cesium carbonate → HCID 66575773, compound

HRID 240485Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][N:3]=1.[NH:16]1[C:20](=[O:21])[CH2:19][CH:18]2[CH2:22][CH2:23][CH2:24][N:17]12.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:10]1([C:9]#[C:8][C:5]2[CH:6]=[CH:7][C:2]([N:16]3[C:20](=[O:21])[CH2:19][CH:18]4[CH2:22][CH2:23][CH2:24][N:17]34)=[N:3][CH:4]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 100 °C

Procedure

(150 mg, 0.58 mmol) 2-Bromo-5-phenylethynyl-pyridine (Example 10, step 1) was dissolved in toluene (2 ml) and (RS)-tetrahydro-pyrrolo[1,2-b]pyrazol-2-one [CAS 1159091-93-6] (73 mg, 0.58 mmol, 1.0 equiv.), cesium carbonate (280 mg, 0.87 mmol, 1.5 equiv.), xantphos [CAS 161265-03-8] (14 mg, 0.02 mmol, 0.04 equiv.) and Pd2(dba)3 (11 mg, 0.01 mmol, 0.02 equiv.) were added under nitrogen. The mixture was stirred for 3 hours at 100° C. The crude product was purified by flash chromatography by directly loading the toluene mixture onto a silica gel column and eluting with an ethyl acetate:heptane gradient 0:100 to 100:0. The desired (RS)-1-(5-phenylethynyl-pyridin-2-yl)-tetrahydro-pyrrolo[1,2-b]pyrazol-2-one (17 mg, 9% yield) was obtained as a light brown solid, MS: m/e=304.1 (M+H+).

Workup

customThe crude product was purified by flash chromatography
washeluting with an ethyl acetate

Sources & evidence

ORD record: ord-b762042b2e0a4658a7d18eea0fcb0092
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648088B2

Reaction notes

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