Acetic Acid → 1h-Indole-1-carboxylic acid,5-[(dimethylamino)methyl]-,1,1-dimethylethyl ester

HRID 20989

반응식

HRID 20989 반응식
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)=O.[C:12]([O:16][C:17]([O:19]C(OC(C)(C)C)=O)=O)([CH3:15])([CH3:14])[CH3:13].[CH3:27][NH:28][CH3:29].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C.CN(C1C=CN=CC=1)C>[CH3:27][N:28]([CH2:1][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:19])[CH:7]=[CH:6]2)[CH3:29]

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 674DimethylamineHCID 90495Di-tert-butyl dicarbonateHCID 589040Indole-5-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 684919351h-Indole-1-carboxylic acid,5-[(dimethylamino)methyl]-,1,1-dimethylethyl ester수율 36.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6342Acetonitrile용매

실험 절차

In a similar manner to Step 1 of Reference Example 4, 5-formylindole (5.27 g, 36.3 mmol) was dissolved in acetonitrile (100 mL), and the solution was treated with di-tert-butyldicarbonate (9.17 mL, 39.9 mmol) and DMAP (44.0 mg, 0.360 mmol), then the mixture was treated with 51% aqueous dimethylamine solution (72.0 mL, 724 mmol), acetic acid (41.6 mL, 727 mmol) and sodium triacetoxyborohydride (46.2 g, 218 mmol), followed by purification by slurry using diisopropyl ether to obtain 5-(dimethylaminomethyl)-1-(tert-butoxycarbonyl)indole (3.61 g, yield 36%).

후처리

  1. customfollowed by purification by slurry

출처 및 근거

ORD 기록
ord-59d0630de42b4180826f17821e743067
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

연결된 노트

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