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Toluene → 4-(2-Methyl-thiazol-4-ylmethoxy)-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

HRID 1929199
Notes
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Reaction equation

HRID 1929199 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][OH:8])[N:6]=1.[CH3:9][CH2:10][O:11][C:12]([C:14]1[N:15]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:16]2[C:21]([CH:22]=1)=[C:20](OCC1C=CC=CC=1)[CH:19]=[CH:18][CH:17]=2)=[O:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>C1COCC1>[CH3:9][CH2:10][O:11][C:12]([C:14]1[N:15]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[C:16]2[C:21]([CH:22]=1)=[C:20]([O:8][CH2:7][C:5]1[N:6]=[C:2]([CH3:1])[S:3][CH:4]=1)[CH:19]=[CH:18][CH:17]=2)=[O:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 10582809(2-Methyl-1,3-thiazol-4-yl)methanolHCID 591526751-tert-butyl 2-ethyl 4-(benzyloxy)-1H-indole-1,2-dicarboxylate

Product 1

HCID 668421144-(2-Methyl-thiazol-4-ylmethoxy)-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(2-Methyl-thiazol-4-yl)-methanol (168, 670 mg, 5.2 mmol) is dissolved in 12 ml of dry THF under argon, followed by addition of 4-Hydroxy-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (102, see example 42, 1.58 g, 5.2 mmol), triphenylphosphine (1.63 g, 6.2 mmol).) and the solution is cooled to 0° C. A 40% solution of ethyl azadicarboxylate in toluene (2.7 ml, 6.2 mmol) is added dropwise and the mixture is stirred for 2.5 h at 0° C. The solvents are removed under reduced pressure and the residue is dissolved in ethyl acetate and washed with sodium hydrogencarbonate solution and brine. The organic layers are dried over sodium sulphate, filtrated and evaporated. The crude product is purified by flash chromatography (silica gel, ethyl acetate/hexanes 3:7)

Workup

  1. customThe solvents are removed under reduced pressure
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with sodium hydrogencarbonate solution and brine
  4. dry with materialThe organic layers are dried over sodium sulphate
  5. filtrationfiltrated
  6. customevaporated
  7. customThe crude product is purified by flash chromatography (silica gel, ethyl acetate/hexanes 3:7)

Sources & evidence

ORD record
ord-0c8a4103f6754916a1d8b8c0e42a152b
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08183366B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes