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Potassium Carbonate → HCID 66693012, 화합물

HRID 472840
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HRID 472840 반응식
[C:1]([O:5][CH:6]([C:11]1[C:12]([CH3:28])=[N:13][C:14]2[N:15]([N:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[CH:20]=2)[C:16]=1Cl)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].[F:29][C:30]1[CH:31]=[C:32](B2OC(C)(C)C(C)(C)O2)[C:33]([CH3:40])=[C:34]2[C:39]=1[O:38][CH2:37][CH2:36][CH2:35]2.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[C:1]([O:5][CH:6]([C:11]1[C:12]([CH3:28])=[N:13][C:14]2[N:15]([N:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[CH:20]=2)[C:16]=1[C:32]1[C:33]([CH3:40])=[C:34]2[C:39](=[C:30]([F:29])[CH:31]=1)[O:38][CH2:37][CH2:36][CH2:35]2)[C:7]([O:9][CH3:10])=[O:8])([CH3:3])([CH3:4])[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 596067662-(8-Fluoro-5-methylchroman-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86670279HCID 86670279, 화합물

생성물 1

HCID 66693012HCID 66693012, 화합물수율 48.9%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물
촉매
HCID 6228Dimethylformamide용매

반응 조건

온도
115 °C

실험 절차

To a 2-5 ml microwave tube was added methyl 2-(tert-butoxy)-2-(7-chloro-2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (200 mg, 0.474 mmol), tetrakis(triphenylphosphine)palladium(0) (55 mg, 0.047 mmol), 2-(8-fluoro-5-methylchroman-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (180 mg, 0.616 mmol), DMF (3 mL), followed by 2M K2CO3 solution (300 μl). The reaction mixture was heated in a microwave reactor at 115° C. for 45 min. The reaction mixture was filtered and the filtrate was purified by silica gel chromatography to afford (128 mg, 48.9%) of the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.82 (s, 1H), 7.76-7.65 (m, 1H), 7.41-7.29 (m, 2H), 7.01-6.73 (m, 2H), 5.02 (s, 1H), 4.37 (dt, J=6.5, 3.5 Hz, 2H), 3.66 (s, 3H), 2.93-2.69 (m, 5H), 2.21 (dd, J=5.6, 2.4 Hz, 2H), 1.86 (s, 3H), 1.18 (s, 9H).

후처리

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-763646432c3b405993e91118c7375441
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08633200B2

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