Triethylamine → HCID 22452629, 화합물

HRID 2185881노트

반응식

HRID 2185881 반응식
[I:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:12]([NH2:14])=O)[C:3]=1[O:15][CH3:16].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[C:12]([C:4]1[C:3]([O:15][CH3:16])=[C:2]([I:1])[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=1)#[N:14]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 22452681HCID 22452681, 화합물

생성물 1

HCID 22452629HCID 22452629, 화합물수율 100.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred, cooled (0° C.) suspension of 4-iodo-3-methoxy-5,6,7,8-tetrahydro-2-naphthalenecarboxamide (2.06 g, 6.22 mmol), triethylamine (2.77 mL, 19.91 mmol), and THF (40 mL) was added trifluoroacetic anhydride (1.23 mL, 8.71 mmol) dropwise via syringe. After addition, the ice bath was removed and the reaction stirred overnight at ambient temperature. The mixture was cooled to 0° C. and excess trifluoroacetic anhydride destroyed with H2O (2 mL). Ethyl acetate (50 mL) was added and the organic layer was washed with H2O (3×25 mL) and brine (25 mL), dried (NaSO4), filtered, concentrated in vacuo and purified by chromatography (100% DCM) to afford a light brown solid (1.96 g, 100%). 1H NMR (CDCl3) δ 7.29 (s, 1H), 4.0 (s, 3H), 2.74 (m, 4H), 1.76 (m, 4H), MS m/z 314 (M+H).

후처리

  1. temperatureTo a stirred, cooled
  2. additionAfter addition
  3. customthe ice bath was removed
  4. temperatureThe mixture was cooled to 0° C.
  5. customexcess trifluoroacetic anhydride destroyed with H2O (2 mL)
  6. additionEthyl acetate (50 mL) was added
  7. washthe organic layer was washed with H2O (3×25 mL) and brine (25 mL)
  8. dry with materialdried (NaSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. custompurified by chromatography (100% DCM)

출처 및 근거

ORD 기록
ord-2f04be89c25841d884870ddf74d9735d
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06403601B1

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