Sodium Carbonate → HCID 58923880, compound

HRID 1364053Notes

Reaction equation

HRID 1364053 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1.Br[C:36]1[CH:45]=[C:44]2[C:39]([C:40]3[N:49]4[CH2:50][CH2:51][CH2:52][N:53]([S:55]([CH3:58])(=[O:57])=[O:56])[CH2:54][C:48]4=[N:47][C:41]=3[C:42]([NH2:46])=[N:43]2)=[CH:38][CH:37]=1>C(O)CC.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:58][S:55]([N:53]1[CH2:52][CH2:51][CH2:50][N:49]2[C:40]3[C:39]4[C:44](=[CH:45][C:36]([C:28]5[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=5)=[CH:37][CH:38]=4)[N:43]=[C:42]([NH2:46])[C:41]=3[N:47]=[C:48]2[CH2:54]1)(=[O:57])=[O:56]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27343783-Pyridinylboronic acidHCID 58923861HCID 58923861, compound

Product 1

HCID 58923880HCID 58923880, compoundYield 17.1%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 10311-PropanolSolvent

Conditions

Temperature
80 °C

Procedure

Sodium carbonate (0.140 g, 1.32 mmol), triphenylphosphine (74.7 mg, 0.33 mmol), 3-pyridine boronic acid (0.149 g, 1.21 mmol), and palladium (II) acetate (25 mg, 0.11 mmol) were sequentially added to a solution of 3-bromo-9-(methylsulfonyl)-9,10,11,12-tetrahydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine (0.450 g, 1.1 mmol) in n-propanol (15 mL), methanol (10 mL), and water (5 mL). The reaction was heated at 80° C. overnight and then concentrated under reduced pressure. The residue was mixed with dichloromethane, and the resulting solid was isolated by filtration. The solid was purified by column chromatography on silica gel (eluting with 2 N ammonia in methanol/chloroform in a gradient from 0% to 25%. The resulting solid was mixed with material from another run and purified again by column chromatography on silica gel under the same conditions to provide 76.8 mg of 9-(methylsulfonyl)-3-pyridin-3-yl-9,10,11,12-tetrahydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine, as a beige solid, mp 302° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was mixed with dichloromethane
  3. customthe resulting solid was isolated by filtration
  4. customThe solid was purified by column chromatography on silica gel (
  5. washeluting with 2 N ammonia in methanol/chloroform in a gradient from 0% to 25%
  6. additionThe resulting solid was mixed with material from another run
  7. custompurified again by column chromatography on silica gel under the same conditions

Sources & evidence

ORD record
ord-a2c1c3a0650f4be19e16a83c70e83589
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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