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

HRID 1797770

反応式

HRID 1797770 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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 calcd for C13H9N2OSI 367.9480).

後処理

  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)

出典と根拠

ORDレコード
ord-4b3142901cbb49dc843ea7451ca74867
出典データセット
uspto-grants-2013_01
特許番号
US08343457B2

関連ノート

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