Cesium carbonate → HCID 59238963, 화합물

HRID 2060963노트

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HRID 2060963 반응식
C([N:8]1[C:20]2[C:19]([OH:21])=[C:18]3[N:22](C(OC(C)(C)C)=O)[C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][C:28]=4[C:17]3=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([F:37])[CH:13]=2)(OC(C)(C)C)=O.Br[CH2:39][CH2:40][CH2:41][NH:42]C(=O)OC(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[F:37][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:20]1[C:19]([O:21][CH2:39][CH2:40][CH2:41][NH2:42])=[C:18]3[NH:22][C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][C:28]=4[C:17]3=[CH:16][C:15]2=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 67212243HCID 67212243, 화합물

생성물 1

HCID 59238963HCID 59238963, 화합물수율 82%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

A mixture of 5,7-diBOC-2,10-difluoro-6-hydroxyindolo[2,3-b]carbazole (4.03 g, 8.0 mmol), tert-butyl 3-bromopropylcarbamate (2.20 g, 9.2 mmol), and Cs2CO3 (10.0 g, 31 mmol), and anhydrous MeCN (120 mL) was heated at 100° C. under Ar until the starting material disappeared (˜2 h). After cooled to RT, the inorganic salt was removed by filtration, washed with dichloromethane, and the combined filtrate was concentrated. The resulting residue 3-(2,10-difluoro-5,7-diBOC-indolo[2,3-b]carbazol-6-yloxy)propan-1-amine was dissolved in CH2Cl2 (100 mL). TFA (10 mL) was added and the solution was stirred at RT overnight. After evaporation, the residue was subjected to chromatography on silica gel, eluting with ethyl acetate/hexane/MeOH (10% cNH3.H2O) (50/50/10-100/0/10), giving 2.35 g (82%) of 3-(2,10-difluoro-5,7-dihydroindolo[2,3-b]carbazol-6-yloxy)propan-1-amine. 1H NMR (400 MHz, DMSO-d6) δ 11.8 (br s, 2H), 8.56 (s, 1H), 7.89 (dd, J=9.4, 2.6 Hz, 2H), 7.44 (dd, J=8.6, 4.6 Hz, 2H), 7.17 (td, J=9.2, 2.4 Hz, 2H), 4.36 (t, J=6.2 Hz, 2H), 2.97 (t, J=6.2 Hz, 2H), 1.98 (pentalet, J=6.2 Hz, 2H).

후처리

  1. custom(˜2 h)
  2. temperatureAfter cooled to RT
  3. customthe inorganic salt was removed by filtration
  4. washwashed with dichloromethane
  5. concentrationthe combined filtrate was concentrated
  6. dissolutionThe resulting residue 3-(2,10-difluoro-5,7-diBOC-indolo[2,3-b]carbazol-6-yloxy)propan-1-amine was dissolved in CH2Cl2 (100 mL)
  7. additionTFA (10 mL) was added
  8. customAfter evaporation
  9. washeluting with ethyl acetate/hexane/MeOH (10% cNH3.H2O) (50/50/10-100/0/10)

출처 및 근거

ORD 기록
ord-069faf33cab945a3980aa1324bdab083
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278341B2

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