Dichloromethane → HCID 58709794, compound

HRID 2375879Notes

Reaction equation

HRID 2375879 reaction equation
I[C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3[CH:17]=[C:16]([C:18]4[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH:23]=4)[NH:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][CH:7]=1.C([N:38]1[CH:42]=[CH:41][CH:40]=[C:39]1B(O)O)(OC(C)(C)C)=O.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>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]>[NH:38]1[CH:42]=[CH:41][CH:40]=[C:39]1[C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3[CH:17]=[C:16]([C:18]4[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:22][CH:23]=4)[NH:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 58710093HCID 58710093, compound

Product 1

HCID 58709794HCID 58709794, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a stirred solution of tert-butyl 4-[4-(3-iodophenylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylate (77.6 mg, 0.15 mmol), N-Boc-2-pyrrolylboronic acid (47.5 mg, 0.225 mmol) and potassium carbonate (41.5 mg, 0.3 mmol) in dioxane/water (4:1) (11.0 mL) was added PdCl2(dppf).CH2Cl2 (12.2 mg, 0.015 mmol). The mixture was heated at reflux for 18 h. Solvents were removed in vacuo and the residue was dissolved in DMF (≈2 mL). The DMF solution was filtered and purified by HPLC to afford the title compound. 1H-NMR(CD3OD, 400 MHz): δ=1.50 (s, 9H), 2.53 (m, 2H), 3.64 (m, 2H), 4.11 (m, 2H), 6.16 (t, J=2.8 Hz, 2H), 6.26 (s, 1H), 6.48 (dd, J=1.2, 3.6 Hz, 1H), 6.60 (s, 1H), 6.81 (dd, J=1.2, 2.8 Hz, 1H), 7.31 (s, 1H), 7.33 (s, 1H), 7.42-7.45 (m, 1H), 7.87 (s, 1H), 8.21 (s, 1H). MS (ES+): m/z 457.08 [MH+]. HPLC: tR=3.15 min (ZQ2000, polar—5 min).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. customSolvents were removed in vacuo
  4. dissolutionthe residue was dissolved in DMF (≈2 mL)
  5. filtrationThe DMF solution was filtered
  6. custompurified by HPLC

Sources & evidence

ORD record
ord-001cbb75d25b468bb3193fd48de9488f
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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