Sodium Carbonate → HCID 67072591, compound

HRID 2098469Notes

Reaction equation

HRID 2098469 reaction equation
[CH3:1][C:2]([CH3:43])([CH3:42])[C@H:3]([NH:30][C:31]([C:33]1[NH:34][C:35]2[C:40]([CH:41]=1)=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])[C:4]([N:6]1[CH2:11][C@@H:10]2[CH2:12][C@H:7]1[CH2:8][N:9]2[C:13]([C:15]1[CH:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][N:16]=1)=[O:14])=[O:5].Br[C:45]1[C:50]([F:51])=[CH:49][CH:48]=[CH:47][N:46]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:51][C:50]1[C:45]([C:18]2[CH:17]=[N:16][C:15]([C:13]([N:9]3[CH2:8][C@@H:7]4[CH2:12][C@H:10]3[CH2:11][N:6]4[C:4]([C@@H:3]([NH:30][C:31]([C:33]3[NH:34][C:35]4[C:40]([CH:41]=3)=[CH:39][CH:38]=[CH:37][CH:36]=4)=[O:32])[C:2]([CH3:1])([CH3:42])[CH3:43])=[O:5])=[O:14])=[CH:20][CH:19]=2)=[N:46][CH:47]=[CH:48][CH:49]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27628032-Bromo-3-fluoropyridineHCID 67215257HCID 67215257, compound

Product 1

HCID 67072591HCID 67072591, compoundYield 14.6%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-{(1S)-2,2-dimethyl-1-[((1S,4S)-5-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]carbonyl}-2,5-diazabicyclo[2.2.1]hept-2-yl)carbonyl]propyl}-1H-indole-2-carboxamide (150 mg, 0.26 mmol), 2-bromo-3-fluoropyridine (69 mg, 0.38 mmol), Pd(dppf)Cl2 (15 mg, 0.018 mmol), sodium carbonate (55 mg, 0.52 mmol) in dry 1,4-dioxane (2 mL) and water (1 mL) was refluxed for 16 h under a nitrogen atmosphere. The solution was concentrated and the resulting residue was purified by reverse phase HPLC. Concentration of the desired fractions containing product afforded the title compound (21 mg) as a pale brown solid. LCMS (m/z): 555.3 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm: 0.90-1.10 (m, 9H), 1.80-2.25 (m, 2H), 3.50-4.30 (m, 4H), 4.15-5.10 (m, 3H), 7.00-7.75 (m, 8H), 7.95-8.70 (m, 3H), 9.00-9.30 (m, 1H), 9.40-9.70 (m, 1H)

Workup

  1. temperaturewas refluxed for 16 h under a nitrogen atmosphere
  2. concentrationThe solution was concentrated
  3. customthe resulting residue was purified by reverse phase HPLC
  4. additionConcentration of the desired fractions containing product

Sources & evidence

ORD record
ord-0dbe627104894b4b85720babe87fa402
Source dataset
uspto-grants-2013_05
Patent number
US08450484B2

Reaction notes

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