Boron tribromide → HCID 67297993, 화합물

HRID 1520386노트

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HRID 1520386 반응식
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[C:14]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[N:13]=[C:12]3[NH:25][CH3:26])[CH:6]=[CH:7][CH:8]=1.COC1C=C(C2C=C3C(=CC=2)N=C(C2C=NC=CC=2)N=C3N2CCCC2)C=CC=1.N1CCCC1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:26][NH:25][C:12]1[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([C:5]3[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=3)[CH:10]=2)[N:15]=[C:14]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[N:13]=1

참가 물질

7

반응물 5

HCID 25134Boron tribromideHCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 67298122HCID 67298122, 화합물HCID 67298534HCID 67298534, 화합물

생성물 1

HCID 67297993HCID 67297993, 화합물수율 99%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a suspension of 6-(3-methoxyphenyl)-N-methyl-2-(pyridin-3-yl)quinazolin-4-amine (prepared in a similar method described for 6-(3-methoxy phenyl)-2-(pyridine-3-yl)-4-(pyrrolidin-1-yl)quinazoline using Scheme 74, substituting N-methylamine for pyrrolidine) (1.00 g, 2.9 mmol) in CH2Cl2 (15 mL) and boron tribromide 1M solution in dichloromethane (8.76 ml, 8.76 mmol) was added at 0° C. The reaction mixture was stirred overnight at room temperature after which it was carefully poured into a vigorously stirring mixture of ice and saturated aqueous solution of NaHCO3. The resultant solid was collected by filtration, dried and then dissolved in a mixture of K2CO3 (2 g) and methanol (50 mL). The solution was then acidified using aqueous NH4Cl solution. (50 mL) and the precipitate which formed was collected by filtration and dried to give 0.95 g of 3-(4-(methylamino)-2-(pyridin-3-yl)quinazolin-6-yl)phenol as pale yellow solid (99%). LCMS m/z=329 (M+1) (Method D) (retention time=1.30 min). 1H NMR (300 MHz, DMSO) δ 9.63 (s, 1H), 9.60 (s, 1H), 8.77 (d, J=8.0 Hz, 1H), 8.74-8.59 (m, 2H), 8.54 (s, 1H), 8.05 (d, J=8.7 Hz, 1H), 7.83 (d, J=8.7 Hz, 1H), 7.54 (dd, J=7.9, 4.8 Hz, 1H), 7.38-7.12 (m, 3H), 6.82 (d, J=7.8 Hz, 1H), 3.17 (d, J=4.3 Hz, 3H).

후처리

  1. customprepared in a similar method
  2. additionwas carefully poured into
  3. stirringa vigorously stirring
  4. filtrationThe resultant solid was collected by filtration
  5. customdried
  6. dissolutiondissolved in a mixture of K2CO3 (2 g) and methanol (50 mL)
  7. custom(50 mL) and the precipitate which formed
  8. filtrationwas collected by filtration
  9. customdried

출처 및 근거

ORD 기록
ord-77845764cbbb4a66a20227e5d6dd54ad
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073890B2

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