Boron tribromide → 2-(3'-Iodo-4'-aminophenyl)-6-hydroxybenzothiazole

HRID 2039387

반응식

HRID 2039387 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([O:17]C)[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[I:19].B(Br)(Br)Br>C(Cl)Cl>[I:19][C:3]1[CH:4]=[C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH:6]=[CH:7][C:2]=1[NH2:1]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 100684372-(4'-Amino-3'-iodophenyl)-6-methoxybenzothiazole

생성물 1

HCID 104516352-(3'-Iodo-4'-aminophenyl)-6-hydroxybenzothiazole수율 61.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-(4′-Amino-3′-iodophenyl)-6-methoxy benzothiazole (5) (8.0 mg, 0.02 mmol) in CH2Cl2 (2.0 mL) was injected 1 M BBr3 solution in CH2Cl2 (0.20 ml, 0.20 mmol) under N2 atmosphere. The reaction mixture was stirred at room temperature for 18 hrs. After the reaction was quenched with water, the mixture was neutralized with NaHCO3. The aqueous layer was extracted with ethyl acetate (3×3 mL). The organic layers were combined and dried over MgSO4. The solvent was then evaporated under reduced pressure and the residue was purified by preparative TLC (Hexanes:ethyl acetate=7:3) to give 2-(3′-iodo-4′-aminophenyl)-6-hydroxybenzothiazole (4.5 mg, 58%) as a brown solid. 1HNMR (300 MHz, acetone-d6) δ (ppm): 8.69 (s, 1H), 8.34 (d, J=2.0 Hz, 1H), 7.77 (dd, J1=2.0 Hz, J2=8.4 Hz, 1H), 7.76 (d, J=8.8 Hz, 1H), 7.40 (d, J=2.4 Hz, 1H), 7.02 (dd, J1=2.5 Hz, J2=8.8 Hz, 1H), 6.94 (d, J=8.5 Hz, 1H), 5.47 (br., 2H). HRMS m/z 367.9483 (M+ calcd for C13H9N2OSI 367.9480).

후처리

  1. customAfter the reaction was quenched with water
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×3 mL)
  3. dry with materialdried over MgSO4
  4. customThe solvent was then evaporated under reduced pressure
  5. customthe residue was purified by preparative TLC (Hexanes:ethyl acetate=7:3)

출처 및 근거

ORD 기록
ord-663f42851aef4c38a8efc505aba3ecd0
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580229B2

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