Water → Methanol

HRID 1912536Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1912536
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:11]3=[N:12][C:13]([CH3:27])=[C:14]([C:23](OC)=[O:24])[C:15]([C:16]4[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=4)=[C:10]3[CH:9]=[CH:8]2)=[C:4]([F:30])[CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:11]3=[N:12][C:13]([CH3:27])=[C:14]([CH2:23][OH:24])[C:15]([C:16]4[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=4)=[C:10]3[CH:9]=[CH:8]2)=[C:4]([F:30])[CH:3]=1.[CH3:23][OH:24]

Komponenten

7

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 71209420methyl 1-(4-chloro-2-fluorobenzyl)-6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

Produkt 2

HCID 887MethanolAusbeute 173,3 %HCID 71209184HCID 71209184, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 1-(4-chloro-2-fluorobenzyl)-6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (250 mg, 0.591 mmol) was dissolved in THF (2 ml). LiAlH4 (2.53 ml, 2.53 mmol) was added to the mixture at 0° C. and allowed to warm to room temperature. The reaction was stirred for 18 hours at room temperature. The reaction was stopped by the addition of 0.1 mL of water followed by a 10 minute wait, then the addition of a 15% NaOH solution (0.1 mL) followed by a 10 minute wait and finally 0.3 mL of water followed by a 10 minute wait. At this point, a fine powder was formed that was filtered out using Celite™ on a frit. The solution was concentrated in vacuo. The chloro was removed partially by the reduction and the mixture of the two compounds was carried to the next step. (1-(4-chloro-2-fluorobenzyl)-6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol and 1-(2-fluorobenzyl)-6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol (202 mg, 0.512 mmol, 47.8% yield) were isolated together as a yellow oil. The crude mixture was carried for the next step. 1H NMR (400 MHz, CHLOROFORM-d) δ=7.44-7.33 (m, 2 H), 7.32-7.19 (m, 3 H), 7.19-6.91 (m, 4 H), 6.28-6.15 (m, 1 H), 5.55 (s, 1 H), 5.49 (s, 1 H), 4.68 (s, 2 H), 2.81 (d, J=4.0 Hz, 3 H), 2.44 (s, 3 H) LCMS (m/z) ES+=361 (M+1) and LCMS (m/z) ES+=395 (M+1).

Aufarbeitung

  1. waitfollowed by a 10 minute
  2. waitwait
  3. waitfollowed by a 10 minute
  4. waitwait
  5. waitwait
  6. customAt this point, a fine powder was formed
  7. filtrationthat was filtered out
  8. concentrationThe solution was concentrated in vacuo
  9. customThe chloro was removed partially by the reduction
  10. additionthe mixture of the two compounds

Quellen und Nachweise

ORD-Eintrag
ord-49de69e8b4f545428c67ea2ff40df840
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609653B2

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