Potassium Phosphate, Tribasic → tert-butyl {3-[4-(2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]oxetan-3-yl}carbamate

HRID 1047041Notes

Reaction equation

HRID 1047041 reaction equation
Br[C:2]1[N:6]2[C:7]3[CH:19]=[CH:18][CH:17]=[N:16][C:8]=3[NH:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:5]2=[N:4][C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC1(C)C(C)(C)OB([C:34]2[CH:39]=[CH:38][C:37]([C:40]3([NH:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[CH2:43][O:42][CH2:41]3)=[CH:36][CH:35]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O>[C:20]1([C:3]2[N:4]=[C:5]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[NH:9][C:8]4[N:16]=[CH:17][CH:18]=[CH:19][C:7]=4[N:6]3[C:2]=2[C:34]2[CH:35]=[CH:36][C:37]([C:40]3([NH:44][C:45](=[O:51])[O:46][C:47]([CH3:49])([CH3:48])[CH3:50])[CH2:43][O:42][CH2:41]3)=[CH:38][CH:39]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 675030133-bromo-2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepineHCID 68067328HCID 68067328, compound

Product 1

HCID 69087676tert-butyl {3-[4-(2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]oxetan-3-yl}carbamateYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 3-bromo-2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine (50 mg) and tert-butyl {3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxetan-3-yl}carbamate (96 mg) and potassium phosphate (82 mg) and PdCl2(dppf)CH2Cl2 (11 mg) in dioxane (2.5 mL) and H2O (0.25 mL) was degassed for 5 min then stirred at 80° C. for 18 h. The reaction mixture was concentrated under reduced pressure. Purification by column chromatography (5-100% ethyl acetate in hexanes) gave the product (58 mg, 81%). 1HNMR (DMSO-d6) 400 MHz δ: 8.57 (s, 1H), 8.16-7.83 (m, 3H), 7.55-7.44 (m, 4H), 7.39-7.21 (m, 7H), 7.15-7.09 (m, 1H), 6.98-6.84 (m, 1H), 6.68 (dd, J=7.8, 4.6 Hz, 1H), 4.87-4.75 (m, 2H), 4.73-4.60 (m, 2H), 1.57-1.03 (m, 9H). LCMS: 558 [M+H].

Workup

  1. customwas degassed for 5 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customPurification by column chromatography (5-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2c9b2002771b4316a200b3bcf4dd6c50
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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