Methyl chloroformate → HCID 57731438, compound

HRID 2234692Notes

Reaction equation

HRID 2234692 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C:7]1[CH:15]=[CH:14][C:13](I)=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[K+].[K+].[CH3:32][O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C:40]1[C:48]2[C:43](=[N:44][CH:45]=[C:46](B3OC(C)(C)C(C)(C)O3)[CH:47]=2)[N:42]([S:58]([C:61]2[CH:66]=[CH:65][C:64]([CH3:67])=[CH:63][CH:62]=2)(=[O:60])=[O:59])[CH:41]=1>ClCCl>[CH3:5][O:4][C:2]([NH:6][C:7]1[CH:15]=[CH:14][C:13]([C:46]2[CH:47]=[C:48]3[C:40]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=4[O:33][CH3:32])=[CH:41][N:42]([S:58]([C:61]4[CH:62]=[CH:63][C:64]([CH3:67])=[CH:65][CH:66]=4)(=[O:60])=[O:59])[C:43]3=[N:44][CH:45]=2)=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])=[O:3]

Participants

7

Reactant 5

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 72911Benzoic acid, 2-amino-5-iodo-HCID 81531DiisopropylethylamineHCID 160390673-(2-Methoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 57731438HCID 57731438, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl chloroformate (0.88 ml, 11.4 mmol) was added to a solution of 2-amino-5-iodo-benzoic acid (2.50 g, 9.5 mmol) and di-iso-propyl ethyl amine (5.96 ml, 34.4 mmol) in dichloromethane (50 ml) and the resulting mixture stirred at room temperature for 4 hours. The solvent was evaporated and the residue used without further purification. MS: m/z 322.1 (M+H+). To this crude was added tetrahydrofuran/acetonitrile/50% w/v potassium carbonate (80 ml), 3-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (4.80 g, 9.5 mmol). This mixture was degassed with nitrogen, split into 4 portions and irradiated in the microwave to 150° C. for 30 min. The reaction mixtures were then combined and extracted with ethyl acetate (3×), dried over magnesium sulfate, and purified by silica gel chromatography to produce 2-methoxycarbonylamino-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoic acid as a white solid. (2.51 g, 46%). MS: m/z 572.6 (M+H+).

Workup

  1. customThe solvent was evaporated
  2. customthe residue used without further purification
  3. additionTo this crude was added tetrahydrofuran/acetonitrile/50%
  4. customThis mixture was degassed with nitrogen
  5. customsplit into 4 portions
  6. customirradiated in the microwave to 150° C. for 30 min
  7. customThe reaction mixtures
  8. extractionextracted with ethyl acetate (3×)
  9. dry with materialdried over magnesium sulfate
  10. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-e6ad00e685f64992ab38f5229c140999
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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