Sodium Carbonate → HCID 178421968, compound

HRID 1618531Notes

Reaction equation

HRID 1618531 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:19]3[C:27]4[C:22](=[N:23][CH:24]=[C:25](B(O)O)[CH:26]=4)[C:21]([CH3:32])([CH3:31])[CH2:20]3)=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1.Cl[C:34]1[N:42]=[CH:41][N:40]=[C:39]2[C:35]=1[NH:36][CH:37]=[N:38]2.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:32][C:21]1([CH3:31])[C:22]2=[N:23][CH:24]=[C:25]([C:34]3[N:42]=[CH:41][N:40]=[C:39]4[C:35]=3[N:36]=[CH:37][NH:38]4)[CH:26]=[C:27]2[N:19]([C:6]2[C:5]3[C:10](=[CH:11][C:2]([F:1])=[CH:3][CH:4]=3)[N:9]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[C:7]=2[CH3:18])[CH2:20]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 53592776-ChloropurineHCID 672849291-(7-Fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)-3,3-dimethyl-2,3-dihydro-1h-pyrrolo[3,2-b]pyridin-6-ylboronic acid

Product 1

HCID 178421968HCID 178421968, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

Prepared according to procedure P using 1-(7-fluoro-3-methyl-2-(pyridin-2-yl)-quinolin-4-yl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-ylboronic acid (25 mg, 0.058 mmol), 6-chloropurine (9 mg, 0.058 mmol), PdCl2(PPh3)2 (4.1 mg, 0.0058 mmol), sodium carbonate (12.3 mg, 0.117 mmol) and heating in the microwave for 1 h at 120° C. After purification 4-(3,3-dimethyl-6-(9H-purin-6-yl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline was obtained as a yellow film. 1H NMR (400 MHz, MeOH) δ ppm 9.27 (1H, br. s.), 8.83 (1H, s), 8.67-8.73 (1H, m), 8.41 (1H, br. s.), 8.01-8.12 (2H, m), 7.92 (1H, d, J=7.8 Hz), 7.83 (1H, dd, J=10.0, 2.5 Hz), 7.52-7.60 (2H, m), 7.48 (1H, ddd, J=9.3, 8.3, 2.5 Hz), 4.06-4.12 (1H, m), 3.95-4.03 (1H, m), 2.33 (3H, s), 1.70 (3H, s), 1.62 (3H, s). Mass Spectrum (ESI) m/e=503 (M+1).

Workup

  1. customPrepared
  2. customAfter purification 4-(3,3-dimethyl-6-(9H-purin-6-yl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline
  3. customwas obtained as a yellow film

Sources & evidence

ORD record
ord-ac2908e1570a4b538efc54d74fb44f72
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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