Nitrogen → (S)-tert-butyl (4-(5-(3-cyano-4-fluorophenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)carbamate

HRID 1891460노트

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HRID 1891460 반응식
Br[C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([F:15])=[C:11]([CH:14]=2)[C:12]#[N:13])=[N:4][N:3]=1.[C:16]([O:20][C:21](=[O:41])[NH:22][C@@H:23]1[C:31]2[C:26](=[C:27](B3OC(C)(C)C(C)(C)O3)[CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1)([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+].N#N>COCCOC.O.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>[C:16]([O:20][C:21](=[O:41])[NH:22][C@@H:23]1[C:31]2[C:26](=[C:27]([C:2]3[S:6][C:5]([C:7]4[CH:8]=[CH:9][C:10]([F:15])=[C:11]([C:12]#[N:13])[CH:14]=4)=[N:4][N:3]=3)[CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1)([CH3:19])([CH3:17])[CH3:18]

참가 물질

7

반응물 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 583672495-(5-Bromo-1,3,4-thiadiazol-2-yl)-2-fluorobenzonitrileHCID 58367258tert-Butyl (S)-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-yl)carbamate

생성물 1

HCID 58367252(S)-tert-butyl (4-(5-(3-cyano-4-fluorophenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)carbamate수율 100%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 18180031Water 1,2-dimethoxyethane용매

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온도
85 °C

실험 절차

Prepared using General Procedure 4. A suspension of 5-(5-bromo-1,3,4-thiadiazol-2-yl)-2-fluorobenzonitrile TDZ INT-3 (1.5 g, 5.3 mmol), (S)-tert-butyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-yl)carbamate IND INT-17 (1.9 g, 5.3 mmol) and potassium carbonate (2.2 g, 16 mmol) in DME:H2O (3:1, 70 mL) was degassed with N2 for 20 min before the addition of Pd(PPh3)4 (0.43 g, 0.3 mmol). The mixture was degassed with N2 for an additional 5 min and the suspension was heated under N2 at 85° C. for 12 h. Upon cooling, the reaction mixture was diluted with water (150 mL) and the mixture stirred for 30 min. The resulting solid was filtered, washed with water, and dried under high vacuum to afford 2.3 g (100%) of crude (S)-tert-butyl(4-(5-(3-cyano-4-fluorophenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)carbamate as light brown solid which was used in the next experiment without purification. LCMS-ESI (m/z) calculated for C23H21FN4O2S: 436.1; found 459.1 [M+Na]+, tR=4.19 min.

후처리

  1. customPrepared
  2. customThe mixture was degassed with N2 for an additional 5 min
  3. temperatureUpon cooling
  4. additionthe reaction mixture was diluted with water (150 mL)
  5. filtrationThe resulting solid was filtered
  6. washwashed with water
  7. customdried under high vacuum

출처 및 근거

ORD 기록
ord-1ced1cc1b151420786ac13dc29946438
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507538B2

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