Benzothiazole-6-carbonitrile → tert-Butyl 4-((6-cyanobenzo[d]thiazol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2174088ノート

反応式

HRID 2174088 の反応式
[C:1]([C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][S:9][C:5]=2[CH:4]=1)#[N:2].CCCCCCC.C1COCC1.C(C1C=CC=CC=1)C.[CH:32]([C:34]1[C:42]([O:43][CH3:44])=[CH:41][C:40]([CH3:45])=[C:39]2[C:35]=1[CH:36]=[CH:37][N:38]2[C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])=[O:33]>C1COCC1.[Li+].CC([N-]C(C)C)C>[C:1]([C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[C:8]([CH:32]([OH:33])[C:34]3[C:42]([O:43][CH3:44])=[CH:41][C:40]([CH3:45])=[C:39]4[C:35]=3[CH:36]=[CH:37][N:38]4[C:46]([O:48][C:49]([CH3:51])([CH3:50])[CH3:52])=[O:47])[S:9][C:5]=2[CH:4]=1)#[N:2]

参加物

6

反応物 3

HCID 10607144Benzothiazole-6-carbonitrileHCID 22742125Tetrahydrofuran heptane ethylbenzolHCID 72191522tert-Butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate

生成物 1

HCID 86701724tert-Butyl 4-((6-cyanobenzo[d]thiazol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 2724682Lithium diisopropylamide溶媒

実験手順

To a solution of 6-cyanobenzothiazol (CAS #:58249-61-9) (54.60 mg, 0.341 mmol) in THF (1.06 mL), LDA in Heptane/THF/Ethylbenzene (205 uL, 0.409 mmol) was added at −78° C. After 20 mins, a solution of tert-butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 19-D) (79 mg, 0.273 mmol) in THF (1.68 mL) was added to the reaction mixture at −78° C. After stirring for 1.5 h, the reaction was quenched with MeOH, sat. aq. NH4Cl solution and brine. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, concentrated, and purified using FCC eluting with Heptane/EtOAc to provide the title compound. MS (ESI−) m/z 448 (M−H).

後処理

  1. customthe reaction was quenched with MeOH, sat. aq. NH4Cl solution and brine
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified
  8. washeluting with Heptane/EtOAc

出典と根拠

ORDレコード
ord-babb7957472c46a49844c1d1331221d8
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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